


Olivia's Date Gone Wrong

by SexTheHex



Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Sun & Moon | Pokemon Sun & Moon Versions
Genre: Anal Sex, Brain Drain - Freeform, Breast Growth, F/M, Futa on Male, Futanari, Oral Sex, Other, Transformation, bimbofication
Language: English
Status: Completed
Published: 2018-08-02
Updated: 2018-08-02
Packaged: 2019-06-20 17:16:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,492
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15539136
Author URL: https://archiveofourown.org/users/SexTheHex/pseuds/SexTheHex
Summary: Sun gets lucky beyond belief and scores a date with the beautiful island kahuna Olivia! How does a guy like him score a date like that? Well, there might be a bit of big, throbbing baggage attached…





	Olivia's Date Gone Wrong

**Author's Note:**

> Originally posted on tumblr on June 17th.
> 
> This was a collab with the artist donkaqq! You can check out the amazing art they made to go with the piece here: http://sexthehex.tumblr.com/post/174982466181/

Sun looked on nervously at his date from across the table. “S-so, this is your favorite place to eat, huh?”

“Sure is!” Olivia replied. “Great food for a pretty good price! I’m so happy to finally be dating again after so long!”

God, Olivia was luscious! Such plump lips on that darling face, such perfect skin… such ample cleavage exposed for the whole world to see. Ooh, and her amazing thighs! Sun couldn’t see them now that they were seated at their table, but the look of those meaty thighs wrapped in those tight shorts nearly had him arriving at his table with a tent pitched. Sun was enthralled. Olivia knew what she had and boy did she love to flaunt it.

Sun was hoping she’d flaunt it a bit more in private later tonight. Everyone knew Olivia was still somehow single, despite all she was rocking. Rumors seemed to suggest Olivia was the type to fuck on a first date. Given how flirtatious the walk here was and how much she seemed to love showing off that booty, Sun was over the moon. He was inches away from fucking an Alolan beauty queen!

Oh how thankful he was for the rumor mill pushing him here! Never in a million years would he have thought he could just walk up to Olivia and ask her out. Who knew she was that desperate? It was all almost as outlandish as that ridiculous rumor he heard flying around. Something about how Olivia was still single for a reason and he’d regret a date with her and… yadda yadda. Sun didn’t remember much in the way of specifics for that one. Frankly it sounded all too ridiculous to even be remotely true.

“Can’t believe the same person who took my trial all that time ago is taking me on a date! You’ve matured really nicely, Sun.” complemented Olivia.

“I appreciate it!” Sun remarked. He instantly sprung to shoot a compliment back to Olivia.

“You… you’ve got such great… “ Sun’s attempt at speech was interrupted by a sudden surge of dizziness.

Olivia’s smile instantly turned to a nervous stare. It wasn’t a look of concern for Sun so much as it was panic at a resurging memory coming back to the forefront of her mind.

“Wh-what’s wrong Sun?” Olivia asked.

“I… Gah, sorry! Something just sort of washed over me!” Sun remarked.

Olivia’s concern started to fade. “Ah, I see! Nothing serious th-”

And right back into panic Olivia went. She could have sworn when Sun blinked, his eyelids looked rosey. Her suspicions were confirmed with another quick blink of Sun’s eye. His eyelids were suddenly as glossy pink as her lipstick!

Oh no… oh no it was happening again!

Olivia tried to end things before they got any worse. “Sun, I think you’ve been a great date this evening, but-”

“Great hair!” Sun replied. “That was it. Great hair. Gosh, you must take such great care of it…”

Sun seeped into his chair, still looking a little out of it. Olivia looked on in concern. Maybe that was the end of it? Maybe her attempt to end the date was enough to stop all the rest from happening?

Before Olivia’s very eyes, Sun’s hair color began to shift. The greyish black head of hair underneath his cap started turning to a strawberry blonde.

That was it! This needed to end immediately!

“Sun, I’m sorry, but for your own good I’m going to have to end our date.” Olivia spoke.

Sun barely registered what Olivia had said. He couldn’t really focus on her words or even the sensation of his facial features changing. All he could really focus on was a headache making him go all dizzy. Was it the food? All Sun had eaten so far was a bread roll. He felt dazed and confused, sapped of most of his energy. His body started to tingle.

“Olivia?” Sun began. “Man, I feel funny…”

Sun slumped in his chair and started taking deep breaths. He fully gave in to the strange tingle that seemed to be radiating through him from head to toe. It felt so hard to focus all of a sudden. His brain felt overpacked! It was like his thoughts were squeezed tight as could be, with nowhere for everything to go.

A lot of important Pokemon knowledge seemed to be seeping out of his head. Type match ups, pokedex information, Pokemon movepools… everything seemed to be sloshing around in his mind, spiralling around some sort of drain to make room in his head and cure that headache. And in place of all that knowledge? Giggles. Silly little quick thoughts intermixed in a space of nothing. Sun’s look of discomfort started to melt away into a big, goofy smile. Without even realizing it, girly little laughs seemed to slip out of his lips.

He could almost feel that warm sort of liquid in his brain draining out and pooling… somewhere.

What’s more, Sun’s memory seemed to be going a little hazy. He could have sworn earlier today he’d dressed in his normal favorite striped shirt. He was almost certain he was wearing it just a moment ago! But, when sun looked down at his chest, this didn’t look exactly like his shirt. No, this was some skimpy version of that article of clothing that barely constituted as a rag. It left his shoulders and upper back naked. It left a generous chunk of midriff expose and seemed to just barely cover his breasts.

…Wait. Breasts?

A glance down and Sun’s smooth muscular chest was no more. Instead, sizable tits were plastered against his chest. Like his clothing before hand, Sun’s mind attempted to deduce if he actually ever had breasts before. He couldn’t recall. Just a seed of worry started to sprout that he could remember something so basic about his anatomy, but it was quickly drowned out by a few more silly giggles. His laughter and that sweeping sensation crawling down from his head towards his toes made him feel so relaxed.

How had he forgotten he’d dressed so sluttily today? It was almost concerning… ah, but the more he worried the more his brain just sort of wanted him to giggle. And all those happy little laughs escaping him made all that anxiety melt away. He sounded so funny giggling, he thought. His voice sounded so much lighter than he remembered. Even his mouth felt weird, like each word carried extra weight to it. Maybe he’d done his lipstick incorrectly? Did he even wear lipstick? He gave a quick kiss of the back of his hand to check. …Yup! Lipstick was on his big puffy lips, the same bright pink shade he always wore while out.

Olivia looked on in panic. Sun’s body was changing right before her very eyes! His masculine frame was rapidly contorting into a slutty girly body! Already his face looked like a dollar whore’s and his chest was still ballooning larger and larger by the second!

Olivia should have known better than to go on this date. She’d hoped this godforsaken ridiculous curse would just go away, but that clearly wasn’t the case.

Damn those island guardians! If Olivia had known that being an Island Kahuna and trial leader made it so the resident Tapu kept her single, she would have never signed up! But no, the deities of the island thought having a relationship interfered with her duties too much. Every single one of her dates had been mercilessly converted into whorish bimbo femboys destined to whore themselves out to horny men instead of settle down with her. This was ridiculous!

And worse yet… Olivia almost enjoyed it at times. Part of that curse to keep her single involved a simple pair of cock and balls replacing her vagina to deter men from even fucking her at all. Sure, they started out small when Olivia was first “gifted” them, but the more men feminized by her curse, the longer, thicker, and harder it all got. Each men’s masculinity had to go somewhere when they were turned into busty boy sluts. It usually just poured into her and enhanced her lower body into an even more distorted form. Now, with over a half dozen men drained, her balls were gurgling, fist sized nuts overflowing with sperm. Her cock rivaled her forearm in size, and many an evening ended with her stroking it for hours.

She felt bad seeing another loser trainer turning into this just from wanting a piece of her. However, she couldn’t deny looking at her date morph into a another slutty bimbo boy right before her eyes had her heaving erection right back to attention. Olivia could feel Sun’s masculinity pouring into her, pumping her obscene cock meat even larger.

Sun had a far less easy time making sense of what was happening to him. His silly little bimbo brain was suddenly lacking all those helpful adjectives to describe how he felt. All he really knew was he felt “tingly”. Also, his butt felt “super tingly”. Indeed, a glance down and he could see why. His ass was expanding into a voluptuous bottom that rivaled even the fattest asses in Alola. All of that bulky upper body weight of his that wasn’t breast tissue seemed to be converting into ass tissue. His adventuring shorts soon looked more like short shorts as the stretched and strained from the size of his morphing bottom and thickening thighs.His hips had to be far wider than his shoulders now!

The only part of his lower half that didn’t seem to be gaining mass was the bits of him clamped between his meaty legs. His once respectable cock length was starting to wilter into a pathetic little pecker. Balls so small they look as though they might be fully impotent complimented the look, reducing his manhood to a miserable shadow of itself.

Finally that annoying tingle seemed to be going away. All that was left was the tingle in his chest and at his feet. Below the table, his shoes were morphing into full blown gold high heels from the insidious magic. Sun hardly even realized that was happening. He was far too transfixed on his ballooning chest, still growing larger and larger… gosh, they looked as big as his head! And gosh, they felt so good to touch…

The odd sensation finally left Sun. Once again, he felt good as new. Appropriate for just how new this version of Sun was. The once proud Pokemon trainer was now a stacked, sexed up parody of his old self, dolled up in bright pink makeup with an ass that had no rivals.

Olivia looked around. Somehow, none of the other diners had seen the minor miracle that had just happened. Nor did anyone seem to notice the bulbous erection in her pink shorts.Olivia had to get Sun out of here before anyone noticed. Surely they’d wonder where this street hooker came from soon.

A plan hatched. There was a single person bathroom across the room for them. Perhaps they could just stay in there until the restaurant’s activity had died down? Surely they couldn’t get out of here before someone noticed the bulge in Olivia’s pants or Sun got on his knees and started shoving his face in people’s crotches.

“Hey Sun…” Olivia began. “How about we go to the bathroom together?”

Sun offered giggles as a response. Olivia took it as a yes.

The Kahuna yanked the trainer’s hand up and out of his seat. Instantly she was taken aback by the size of his rump, now fully on display having emerged from beneath the table. Her own lower half surged to life.

“Shit!” Olivia yelped as she realized her erection was about to emerge from her shorts’ leg hole.

Olivia hurried Sun towards the opposite side of the room as quick as she could. Just the small trek a few yards away was a total nightmare as the two’s anatomy pushed their clothing to its limits.

Oh no. Olivia felt the worse happen. Her cock had completely slipped out! Situated against her right thigh was a bulging, throbbing hunk of dark meat ready for action. The moment she realized what was happening, she broke into a run. Sun was yanked along for the ride, but his legs simply couldn’t keep up. The sound of tearing denim pierced the air as Sun’s shorts ripped wide open around his fat ass! Now heads had finally started to turn towards them. The other customers of the shop got a clean look at Olivia and Sun diving into the single person bathroom together. Olivia was about to die of embarrassment.

The bathroom door locked. Olivia attempted to assess the situation. Sun couldn’t come back out of here at all with that rip in his pants. Olivia couldn’t fit her anaconda into her shorts unless she dealt with her urges. What were they to do?

Something clicked in Sun once he realized he was in a private space with Olivia. He realized just what might be possible now that the two were alone. A little spark in his ditzy little head vaguely recalled his hopes from earlier, that he might have a chance at fucking Olivia.

Some relic of memory in his head told him he should look up and down that wicked hot body of hers and get in the mood. Examine her chest, face, ass… but Sun found it very hard to focus on these features this time. Instead his feminization had left his eyes staring hungrily at that pulsating, fat manhood situated between her legs. A perfect fucking machine, even larger than before thanks to the curse contributing some of his manhood.

Sun still wanted a night with Olivia. His tongue was already licking his lips at the prospect of smearing his pretty makeup all up and down that heavenly shaft. His tiny cock flexed and let a bit of pre loose as he imagined what it’d feel like to have that ruin his ass and take his anal virginity… Sun was horny. He needed to be mounted. Now. his body demanded it, and there was little left in him to fight against it.

Sun broke away from the panicked Olivia and climbed aboard the sealed toilet seat. He rested his knees on the seat while he pressed his upper half and titanic tits against the porcelain back. His body needed it. His body demanded he be presented for a good fucking this instead.

Sun meekly spoke up. “Ehehehe… I know it’s the first date and all but like…Do you wanna do it?”

Oh no. Olivia’s cock was at full mast. Any guilt for doing this to Sun was rapidly transitioning into delighted excitement. Was she really about to do this? I mean, the curse had already had its way with Sun. She’d only be giving them what they both wanted at this point. Surely his horny little bimbo brain just ached for a cock to teach him what it was like to get fucked. Surely he knew all those dreaded rumors about her and knew something had to be amiss. Oh, but she hadn’t even kissed him and here she was plotting to wreck his asshole wide as could be with her dick.

The longer she stared at that ass, the quicker those inhibitions drained to nothing. Olivia decided Sun at least deserved a kiss.

Olivia planted her knees against the ground and thrust her face forward into that bulge mass of bimbo boy bottom. Her plush mouth dove straight for Sun’s puckered anal lips. In a deep kiss, she planted her lavender pink lipstick all over the messy orifice. Into Sun’s anal passage her long wet tongue dove, flicking back and forth with masterful strokes.

Sun’s smile turned goofy as he felt the warm heat of Olivia’s tongue prod around inside him. Ooh gosh, this felt lovely. So natural… what a way to lose his anal virginity! He could see himself getting very use to having all manner of things shoved inside him. Sun pressed his heaving chest back against the toilet and let his body melt from Olivia’s tongue work.

For what felt like ages, Olivia kissed and delighted in that fat femboy ass. Lavish kissing all over his asshole paired nicely with pretty kisses painting his dick up and down. Their only interruption came from a knock at the door, to which Olivia gave a prompt “Fuck Off!” and resumed delighting in that fat rump.

But soon the time came when both wanted more. Sun had had his first taste of anal and Olivia had had more than enough a tasting of Sun’s ass. It was time to get to the real thing. A proper round of fucking to break in Sun’s new bimbo body. Ball draining, ass stretching, feverish primal fucking, fueled by that mammoth erection of Olivia’s.

Olivia gave Sun’s ass a smack. “So you want it?”

“Mhmm~” Sun replied in a daydreamy groan, still delighted from the analingus.

Olivia grasped on to Sun’s cheeks. “C’mon! Louder than that! Say it like you mean it!”

Getting manhandled set Sun’s libido ablaze. “Fuck me! C’mon, ruin my ass already!”

Olivia’s teasing only got worse. She loomed over Sun, drawing near and pressing her impressive bust against Sun’s back. Her cock sat between his plush rump, glans pressing riiight against that puffy hole, ready to shove in at a moment’s notice. Sun felt hotter than he’d ever felt in his life. He’d do anything for her now. And Olivia knew that far too well.

Olivia whispered into Sun’s ear. “Beg.”

“Fuck meee~! Fuck my faggot ass as hard as you can! Knock me up with that fat dick, please oh please! Fuck me, fuck me, fuuuuck meeee~!” Sun whimpered.

“Good girl~” Olivia purred.

Neither could wait any longer. Olivia’s cock sunk into Sun’s needy asshole, slowly going deeper and deeper into his fat ass. Olivia was grunting with gritted teeth as she felt Sun’s inner walls squeeze her tight. Sun was a moaning wreck, letting whorish outbursts of noise shout out of his lips to reverberate around the tight bathroom. Those yells turned louder and more desperate as Sun felt the kahuna’s monster cock sink increasingly deep inside him. It felt like it was poking against his stomach at this point! Heavy pants left Olivia as more and more and more submerged into him.

There it was. Down to the hilt. Balls deep, Olivia’s fertile nutsack dwarfing Sun’s pathetic sissy balls. Sun was in disbelief something that huge could fit inside him. Just as shocking, somehow it wasn’t painful. It felt… it felt good. It felt wonderful to have hot pulsating dick meat claiming his insides like sex toy. Sun started to piece things together. He really wasn’t much of a man anymore, just a total bimbo whore. All he really wanted was for a stronger cock to claim his slutty body and use him like a proper sex toy.

Olivia kept herself lodged deep in Sun’s inside. Now her urges transformed once again as she realized just how much power she had over her little brainless bimbo. Her hands slipped forward and under the stretched remains of Sun’s shirt towards his tender nipples. Each hand grasped the sensitive bits before groping each breast with an open palm.

“Damn, you’re as stacked as I am!” Olivia commented. “Gotta admit, I’m a bit jealous of that ass of yours too. Bigger than mine!”

Slowly Olivia withdrew her fat dick from Sun’s anal passage as she continued speaking.

“At least I’ve still got the bigger cock~ This ought to be fun!”

Right back into Sun’s needy asshole her shaft dove, only withdrawing maybe half the length of the giant rod before slamming back in and full force.

“Fuck, fuck! F-fuck!” Sun protested at the sensation. This was too much! But oh, how rapidly that reaction was fading away into delight. How easily his cock hungry brain warped any worry of have such a huge dick inside him into sheer delight. The trickle of “Fuck!” continued from Sun’s makeup covered face, but with a tone that implied less astonishment and more needy begging.

Olivia, meanwhile, was having the time of her life. His ass was even better than the faggot she accidentally feminized last time! She would have felt bad thinking that any other time, but having hormones from her oversized balls flood her system to power that inhuman fuckrod of a cock was turning her into an animal. All she really wanted was to scratch that primal itch and reach climax. She wanted to properly breed this boycunt until it was claimed by and leaking her white hot seed.

But the kahuna was hardly a quick shot. No, even an ass squeezing her this tight, borderline milking her dick, wouldn’t cause her to pop just yet. Poor Sun was just now realizing the pleasures of his ass. What sort of lover would she be if she didn’t give him the time of his life and drive him to his first hands free assgasm? Minutes and minutes of pumping passed. Olivia was relentless. Constantly little teasing quips were whispered right into Sun’s ear. Plenty of “Good girl, good girl~!” and “Do you like your new life, bitch?” rang out of her. Sun was enthralled the entire time. He was a moaning mess that delighted in every little touch Olivia offered his body.

“Gnngh…” Sun grunted. Something felt odd. A sudden hot flash hit him. He felt… he felt wonderful! Ecstatic! Oooh, he felt so good! His grunting turned to gasping as his body moved on its own. His cock flexed and pulsated in rhythm with Olivia’s fucking. He was having his first anal orgasm!

Unceremoniously, his cock gave a pathetic little jerk, a motion more fitting for someone about to pee than climax. Watery strands of semen started to dew out of the tip of his cock, drooping onto the toilet seat little by little. More concentrated droplets trailed out him with every pump Olivia gave. Sun was having the cum fucked right out of his, his tiny little clit of a cock and his wimpy nuts not even able to pump his out cumshot out of him without a fat dick doing all the work.

Sun groaned in delight at the sensation. Olivia withdrew just for a moment to see what all the fuss was even about. Her eyes were greeted with a handful of drops of cum on the porcelain below.

“Ooooh, how cute!” Olivia gushed. “Your first girl orgasm! Feels great huh? Well, get used to it. No woman’s ever gonna want that sad thing in them. Just learn to love cumming with your ass, honey~”

Olivia reentered Sun, yet again violating him until her meaty balls slammed against his cock.

“Got it?” She asked.

“Yes ma’am!” Sun happily barked.

“Good! Good.” Olivia replied. “Now, it’s time I got off.”

It was Olivia’s turn. Sun was suddenly stunned. Olivia’s pace… oh god, all of a sudden it was brutal! No longer was she treating him like an anal first timer, now she was treating him like a full blown anal bitch! With a ruthless pace, Olivia slammed in and out of her little bimbo whore. There was hardly any worry now. She knew he could take it, it was just a matter of breaking him in.

Sun was in heaven. The boy was openly moaning obscenities, tongue hanging, eyes creeping into the back of his skull. Everything about this was heaven. God, he loved being Olivia’s anal slut! Already his greedy, cock hungry brain was looking forward to the next time Olvia fucked him raw. Hell, why stop at just Olivia!? Why not whore himself to as many people he could and sample all of their fat fucking dicks? Surely there had to be others as hung as Olivia out there. Oooh, Sun was going to drain every cock in Alola in his boypussy!

And his journey would all start with Olivia. She was close. Faster still she went. The sound of her naked flesh pounding against his fat ass filled the tiny bathroom. She leaned in back close, bearing her weight against the bimbo femboy. Soon she was a grunting mess. Orgasm was so close. Oooh, she was going to stain his insides white! Just a little close. Just a little bit more of that whore squeezing her. Just a bit more squeezing his massive fucking cow tits. Just one last girly whimper begging for more…

O-Oh! That was it! She was there!

One final pump, one last deep shove into Sun’s bowels and she was finally there. Hot gooey cum blasted out of her at an incredible volume, one fitting for her gargantuan ballsack. Sun could feel it. He was being bred. He was getting used like the stupid sex toy he was… Wow did he love it. Getting claimed by someone bigger and stronger than him felt amazing. He loved this. He already wanted more, and Olivia was still nutting inside of him!

Soon cum started to backwash out of Sun’s backside, escaping between what little space existed between Sun’s distended hole and Olivia’s massive cock. Just the amount leaking out from that alone dwarfed Sun’s wimpy anal orgasm from earlier. When Olivia was finally done, when all of her cock’s love had poured out of her into that ruined hole and when she finally withdrew from his anal folds, the sight was something to behold. Sun was ruined. His gaping asshole slowly dripped cum as he desperately tried to clench the orifice back shut. He couldn’t seem to do it.

“Sorry about the whole ruining-your-asshole thing.” Olivia half seriously apologized.

“Hmmm? Oh, whatever.” Sun replied. He really couldn’t care less about his anus publicly displaying he was a willing cum dump. If anything, the odor from Olivia’s spunk wafting out was the advertisement he wanted.

Olivia was settling back down to reality and coming to realize they’d made a suspicious amount of noise in the tiny bathroom. Getting out of here now that Sun’s clothes were ruined would be an ordeal. How were they suppose to…

Oh?

Olivia was so transfixed on how to get out of here with some subtlety that she’d completely ignored Sun. In that short amount of time, Sun had gotten off of the toilet, sat down on his knees, and situated his face against the darling cock that had just destroyed his ass. His anus was still dribbling cum onto the floor. He couldn’t care; he was far more interested in sinking his lips down Olivia’s titanic shaft.

Ass to mouth already? Gosh, Sun was a total anal slut at heart! Eh, she could worry about getting out of here later. For now, it was time she make this bimbo choke on her cock.


End file.
